Strategy Session: How and When To Push All-in

Bye bye Mike Olt. Hello Jacoby Ellsbury!

The real baseball non-waiver trade deadline is in approximately 6 hours, so it seems like an appropriate time to discuss how to make your push for a championship. Most fantasy league trading deadlines are at some point in August (with a few being today), so if you're sitting in contention, you've probably already either made a deal or two, or have some thoughts of what you want to accomplish. You'll see varied opinions by experts everywhere on how to approach this, and there's really no wrong answer - it's more dictated by personality type than anything else. But just like in real baseball, making a deadline deal in a keeper or dynasty league can have long-lasting implications.

But before we go into this, let me first address the owners whose teams have faltered this year and need to re-load. If you're in a keeper league, I always do the same thing. Identify the players who would currently be keepers on my roster, then sell everyone else if I can improve those current keepers. A dynasty league is a little trickier, as you don't want to sell 2013 and 2014 at the same time you sell 2012. So it's generally expiring contracts and older players who I would put out there. Don't be the guy who falls out of contention and puts Cole Hamels on the block - he's still going to be more valuable in 2015 and 2016 than the prospects you would get back. But Paul Konerko, Lance Berkman and Ryan Dempster? Sure.

Anyway, getting back to the task at hand. My personality type tends to be a little more conservative, so I'm not going to be the owner who deals away every potential keeper on his roster for any minimal upgrade he/she can find. There is definitely a point where the upgrade from Aaron Hill to Brandon Phillips is not worth a $2 Trevor Bauer. You just have to find your own point that you're comfortable with and stick with it - and some of that may have to do with how keepers are valued in your league. I'm going to use a few examples for this, but mostly a pair of trades I made in my most important keeper league yesterday.

For background, this is a 16-tm standard roto keeper league where you keep 7 players and 3 minor league spots from season to season. There's a $260 auction cap and a $330 in-season cap. I'm in first place by 6 points and have been right around that same spot for nearly two months. My offense is good across the board, but needs improvement, mostly in HR and SB. My pitching staff has a nice lead in ERA/WHIP, but could use extra Wins & K's. Right now, the biggest trade chips I have at my disposal are the following: $3 Eric Hosmer, $5 Aroldis Chapman, $8 Edwin Encarnacion, $9 Chris Sale, $11 Starlin Castro, $1 Oscar Taveras, $1 Mike Olt, $1 Xander Bogaerts, $8 Alcides Escobar, $11 Colby Rasmus, $3 Jason Motte and $6 Addison Reed.

Now, I could go completely nuts if I wanted to and deal away guys who should be the backbone of my team for years to come, but there's so much fluctuation in two months' worth of performance, that I try to do two things. First, replace any holes on my roster with good players. Second, target studs as a replacement for any non-studs. And in this case, I did one of each.

Trade 1: $8 Alcides Escobar, $1 Mike Olt and $24 Jayson Werth for $40 Jacoby Ellsbury, $17 Clay Buchholz and $1 Anthony Gose

Trade 2: $1 Xander Bogaerts for $15 Aaron Hill and $1 Josh Collmenter

When viewed as one larger trade, here's what my roster turnover looks like:

Jacoby Ellsbury replaces Willie Bloomquist/Jayson Werth - huge plus in 2012 value

Clay Buchholz replaces Luis Mendoza - huge plus in 2012 value

Aaron Hill replaces Alcides Escobar - slight plus in 2012 value

Josh Collmenter replaces Drew Smyly - slight plus in 2012 value

So basically, I've used two of my three prospects and a good keeper in Escobar (who I would not have kept anyway) to get two huge upgrades. That type of deal was exactly what I was looking for, and it puts me in a position to still deal one of my big guns (Hosmer, Sale, Taveras, Chapman) as the trade deadline gets closer if someone gets hurt or I need to make up some additional ground.

These two-tier trades are one of the best ways that teams can maximize their returns for prospects/keepers that are on the block because sometimes things don't work out perfectly from a positional standpoint with the team that's willing to pay the most for your guy. In this case, the team that was willing to pay the most for Bogaerts was offering up a solid MI - so I found a team needing a MI and leveraged that to get an upgrade elsewhere. And by doing this, you're really channeling the value on your team into other areas. So if you can get a $20 player for Keeper X and you already have a $15 player at that position - dealing that $15 player for an extra $15 of value at a different position will maximize the overall value of your roster. So do your due diligence around your league and focus on what the other owners want rather than what you need. If you do that, you may be able to position yourself better for a championship run.

Follow me on Twitter at @tfw_bret.

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